I can confirm that is Jon Gruden. I saw him at a distance spinted closer to verify. He spotted me and said "dont start any rumors.young man". Then he got on a flying unicorn and off he went. It was him, im.positive! Smokey was freakin out over the unicorn. Howling like a mother.
OP here. Someone tweeted that he was at Webb this morning speaking with the principal. I believe 2 out of his 3 kids have not graduated. also, he came into my work a few years ago for the Condredge Holloway premiere and the height difference between him and Cindy is pretty spot on.
And of course, it's twitter so take it with a grain of salt.